Thread by @businessbarista

Today, Morning Brew is a 110-person, 8-figure media brand.

But back in 2015, it was a shitty PDF with a couple hundred readers.

That's why taking the leap into entrepreneurship was so difficult.

Here’s how I made the big move 🧵

Let's set the stage.

It's July 2015 & I just started my trading job at Morgan Stanley in NYC.

I was living the dream.

Dream job.
Dream city.
Dream situation.

You have to understand.

I was born to be in Finance.

Dad worked in Sales & Trading.
Mom worked in Sales & Trading.
Grandpa worked in Sales & Trading.

And I wanted to be just like them.

But three months into my job, my heart was saying something different than my head.

My head said, "This is your dream job, appreciate this amazing opportunity."

My heart said, "Something feels off. This doesn't feel like a dream job should feel."

It took time to figure out, but I realized why I felt off.

I had lost my secret weapon.

You see, throughout school I attributed my success to one thing: work ethic.

I wasn't smarter than everyone.

But I outworked everyone.

That changed once I started my job in Finance.

Here was my typical day:

5:15 - wake up
5:30-6:00 - commute
6:00-6:45 - work out
7:00-7:30 - day job in Trading
7:30-8:00 - commute
8:00-8:30 - dinner
8:30-sleep - Morning Brew

I was diluting myself.

If I wanted to be the best trader, I'd spend every waking hour trading.

If I wanted to be the best founder, I'd spend every waking hour on the Brew.

But I was doing neither, and felt like I was doing a B- job at both.

That ultimately brought me to a crossroads.

I could no longer take this feeling of inadequacy & the anxiety that came with it.

I had to make a decision:

1) Stay at Morgan Stanley & Stop Morning Brew

2) Quit Morgan Stanley & Start Morning Brew Full-Time

And how I made the decision was to look through three lenses:

1) The lens of regret
2) The lens of life
3) The lens of options

THE LENS OF REGRET

I asked myself a simple question.

What would future Alex regret more?

1. Leaving Morgan Stanley, Morning Brew failing, and having to find a job.

2. Staying at Morgan Stanley & watching someone build a Brew competitor

My answer was a no-brainer: #2

THE LENS OF LIFE

Losing my dad suddenly in college forced me to see the world differently.

It made me appreciate what matters & face life's fragility.

I was rewired to optimize time for fulfillment & purpose.

Morning Brew gave me far greater purpose than Morgan Stanley.

THE LENS OF OPTIONS

I asked myself a second simple question.

"If Morning Brew fails, then what?"

And then I went through all the options...

1) Go back to Morgan Stanley
2) Join another startup
3) Go to business school
4) Join a media company
5) Find job via my network

With lenses in hand, I was ready to make a decision.

On August 15, 2016, @austin_rief & I met up at Pete's Tavern in NYC to talk about the future.

We went into the bar not knowing what we'd do.

We left the bar knowing we'd go all-in on Morning Brew.

A few final points I want to make:

1) This was any incredibly difficult decision. It may sound easy, but I was lost & anxious for 8 months.

2) My privilege made this decision far easier. Money wasn't a limiting factor of quitting, so I could take the leap way easier.

And this is how I made the leap!

For my full story quitting a cushy job in Finance, listen to my episode of Founder's Journal: bit.ly/3y6AIVt

Finally, follow @businessbarista for more stories on career, business, and startups.